NAV

Talbutal

Identification

Generic Name
Talbutal
DrugBank Accession Number
DB00306
Background

Talbutal, also called 5-allyl-5-sec-butylbarbituric acid, is a barbiturate with a short to intermediate duration of action. Talbutal is a schedule III drug in the U.S.

Type
Small Molecule
Groups
Approved, Illicit
Structure
3D
Similar Structures
Weight
Average: 224.2563
Monoisotopic: 224.116092388
Chemical Formula
C11H16N2O3
Synonyms
  • (RS)-5-allyl-5-sec-butylpyrimidine-2,4,6(1H,3H,5H)-trione
  • 5-allyl-5-sec-butylbarbituric acid
  • sec-Butyl allyl barbituric acid
  • Talbutal
  • Talbutale
  • Talbutalum
External IDs
  • HSDB 3397
  • WIN 5095

Pharmacology

Indication

For use as a sedative and hypnotic.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Talbutal is a short to intermediate-acting barbiturate that is a nonselective central nervous system (CNS) depressant. As with other barbiturates, talbutal is capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. Barbiturates may also induce anesthesia at sufficiently high therapeutic doses.

Mechanism of action

Talbutal binds to GABAA receptors at a distinct binding site associated with a Cl- ionopore of the receptor. Upon binding, talbutal increases the duration of time for which the Cl- ionopore is open, leading to prolonged inhibitory effect of GABA at the postsynaptic thalamic neuron.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-2
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-3
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-4
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-5
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-6
potentiator
Humans
AGABA(A) Receptor
positive allosteric modulator
Humans
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Humans
UNeuronal acetylcholine receptor subunit alpha-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UGlutamate receptor 2
antagonist
Humans
UGlutamate receptor ionotropic, kainate 2
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Acute barbiturate poisoning is associated with symptoms such as drowsiness, confusion, coma, respiratory depression, hypotension, and shock.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Talbutal is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Talbutal is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Talbutal is combined with Acetophenazine.
AclidiniumThe risk or severity of adverse effects can be increased when Talbutal is combined with Aclidinium.
AgomelatineThe risk or severity of CNS depression can be increased when Talbutal is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Talbutal is combined with Alfentanil.
AlimemazineThe risk or severity of CNS depression can be increased when Talbutal is combined with Alimemazine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Talbutal.
AlmotriptanThe risk or severity of CNS depression can be increased when Talbutal is combined with Almotriptan.
AlosetronThe risk or severity of CNS depression can be increased when Talbutal is combined with Alosetron.
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Food Interactions
Not Available

Products

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International/Other Brands
Lotusate (Sanofi Aventis)

Categories

ATC Codes
N05CA07 — Talbutal
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Barbituric acid derivatives
Alternative Parents
N-acyl ureas / Diazinanes / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1,3-diazinane / Aliphatic heteromonocyclic compound / Azacycle / Barbiturate / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Hydrocarbon derivative / N-acyl urea
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4YIR8202AX
CAS number
115-44-6
InChI Key
BJVVMKUXKQHWJK-UHFFFAOYSA-N
InChI
InChI=1S/C11H16N2O3/c1-4-6-11(7(3)5-2)8(14)12-10(16)13-9(11)15/h4,7H,1,5-6H2,2-3H3,(H2,12,13,14,15,16)
IUPAC Name
5-(butan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
SMILES
CCC(C)C1(CC=C)C(=O)NC(=O)NC1=O

References

General References
Not Available
KEGG Drug
D06887
PubChem Compound
8275
PubChem Substance
46507821
ChemSpider
7976
RxNav
89810
ChEBI
134923
ChEMBL
CHEMBL1200802
Therapeutic Targets Database
DAP000670
PharmGKB
PA164779051
Wikipedia
Talbutal

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)109 °CPhysProp
water solubility1810 mg/L at 25 °CMEYLAN,WM et al. (1996)
logP1.47HANSCH,C ET AL. (1995)
pKa7.79 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility2.46 mg/mLALOGPS
logP1.87ALOGPS
logP1.59Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)7.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.27 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity58.05 m3·mol-1Chemaxon
Polarizability22.48 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9272
Blood Brain Barrier+0.984
Caco-2 permeable-0.5931
P-glycoprotein substrateSubstrate0.6383
P-glycoprotein inhibitor INon-inhibitor0.5341
P-glycoprotein inhibitor IINon-inhibitor0.9761
Renal organic cation transporterNon-inhibitor0.9352
CYP450 2C9 substrateNon-substrate0.7904
CYP450 2D6 substrateNon-substrate0.9009
CYP450 3A4 substrateNon-substrate0.7245
CYP450 1A2 substrateNon-inhibitor0.8455
CYP450 2C9 inhibitorNon-inhibitor0.8308
CYP450 2D6 inhibitorNon-inhibitor0.9229
CYP450 2C19 inhibitorNon-inhibitor0.7692
CYP450 3A4 inhibitorNon-inhibitor0.8764
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9375
Ames testNon AMES toxic0.6105
CarcinogenicityNon-carcinogens0.8617
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity3.5595 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9879
hERG inhibition (predictor II)Non-inhibitor0.9537
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-00kf-9400000000-724aeaec6df65c3e5931
GC-MS Spectrum - CI-BGC-MSsplash10-004i-0090000000-603a585be8f03eb2145e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Gamma-aminobutyric acid receptor subunit alpha-2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details2. Gamma-aminobutyric acid receptor subunit alpha-3
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details3. Gamma-aminobutyric acid receptor subunit alpha-4
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA4
Uniprot ID
P48169
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight
61622.645 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details4. Gamma-aminobutyric acid receptor subunit alpha-5
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Transporter activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Details5. Gamma-aminobutyric acid receptor subunit alpha-6
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA6
Uniprot ID
Q16445
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight
51023.69 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Details7. Gamma-aminobutyric acid receptor subunit alpha-1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
  4. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  7. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details8. Neuronal acetylcholine receptor subunit alpha-4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details9. Neuronal acetylcholine receptor subunit alpha-7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details10. Glutamate receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ionotropic glutamate receptor activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA2
Uniprot ID
P42262
Uniprot Name
Glutamate receptor 2
Molecular Weight
98820.32 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Details11. Glutamate receptor ionotropic, kainate 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Kainate selective glutamate receptor activity
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIK2
Uniprot ID
Q13002
Uniprot Name
Glutamate receptor ionotropic, kainate 2
Molecular Weight
102582.475 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:06